Welcome to 329 Union Church Road in Chestertown, located in Queen Anne’s County—a home with plenty of space, useful updates, and room to truly make it your own! Situate...

Rarely do vacant parcels like this become available so close to historic Chestertown! Offering approximately 43 acres, this exceptional property presents a unique opportu...

This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property f...

Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added...

Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The pro...

**OPEN HOUSE Sunday September 13th 11AM-1PM** This adorable rancher will soon be at the top of your "favorites" list, with a welcoming interior and plenty to love outside...

Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Dir...

Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch be...

Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. D...

Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a ...

Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peac...

Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary s...

Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is ...

Professional Pictures Coming Soon! Fantastic opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in The Village of Chestertown, offered at a price th...

Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renov...

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for...

Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with...

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The ...

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its...

Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bat...

Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Che...

MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern...

Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excelle...

Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet c...

Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0...

A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Cheste...

Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comforta...

Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy light filled living room, and an eat-in...

Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood...

PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effor...

Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. E...

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and East...

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked ...

4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be s...

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Cheste...

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square ...

Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitch...

Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in ...

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of ...

A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington Col...

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with ...

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, thi...

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natur...

Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, f...

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condomi...

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, lo...

Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, pa...

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly posi...

Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pum...